Memantine → (2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl (3,5-dimethyladamantan-1-yl)carbamate

HRID 2167204Notes

Reaction equation

HRID 2167204 reaction equation
CN1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH:12]=[C:13]([CH3:30])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:29])[CH2:18][CH2:19][CH:20]=[C:21]([CH3:28])[CH2:22][CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])=[O:9])CC1.C(C/C(/C)=C/CC/C(/C)=C/CO)/C=C(/CCC=C(C)C)\C.[CH3:52][C:53]12[CH2:62]C3(N)[CH2:61][CH:55]([CH2:56][C:57](C)([CH2:59]3)[CH2:58]1)[CH2:54]2.C1N=CN(C(N2C=NC=C2)=O)C=1>>[CH3:52][C:53]12[CH2:58][CH:57]3[CH2:56][C:55]([CH3:61])([CH2:7][C:6]([NH:5][C:8](=[O:9])[O:10][CH2:11]/[CH:12]=[C:13](\[CH3:30])/[CH2:14][CH2:15]/[CH:16]=[C:17](\[CH3:29])/[CH2:18][CH2:19]/[CH:20]=[C:21](\[CH3:28])/[CH2:22][CH2:23][CH:24]=[C:25]([CH3:26])[CH3:27])([CH2:59]3)[CH2:62]1)[CH2:54]2

Participants

5

Reactant 4

HCID 4054MemantineHCID 682631,1'-CarbonyldiimidazoleHCID 5281365GeranylgeraniolHCID 781640563,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl 4-methylpiperazine-1-carboxylate

Product 1

HCID 86701131(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl (3,5-dimethyladamantan-1-yl)carbamate

Procedure

Similar to the preparation of 40a, the reaction of alcohol 1 with memantine and CDI afforded the desired compound 41 as a viscous oil. Column (DCM/MeOH); TLC Rf: 0.70 (10% EtOAc/Hexanes).

Sources & evidence

ORD record
ord-75114d30f11e4d4fb08e4bfc9a95b972
Source dataset
uspto-grants-2015_06
Patent number
US09045403B2

Reaction notes

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